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Diaryldiazoketones as Effective Carbene Sources for Highly Selective Rh(II)-Catalyzed Intermolecular C–H Functionalization

Year: 2024
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide A novel donor/acceptor carbene intermediate has been developed using diaryldiazoketones as carbene precursors. In the presence of the chiral dirhodium catalyst, Rh 2 ( S -TPPTTL) 4, diaryldiazoketones undergo highly regio-, stereo-, and diastereoselective C–H functionalization of activated and unactivated secondary and tertiary C–H bonds. Computational studies revealed that the arylketo group behaves differently than the carboxylate acceptor group because the orientation of the arylketo group predetermines which face of the carbene will be attacked.
DOI: 10.1021/jacs.3c14552
Authors: Terrence-Thang H. Nguyen, Aaron T. Bosse, Duc Ly, Camila A. Suarez, Jiantao Fu, Kristin Shimabukuro, Djamaladdin G. Musaev, Huw M. L. Davies
Institution: Emory University
Language: English
Field: Chemistry
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: G1207660340, New Directions in Enantioselective C-H Functionalization, G236029928, MRI: Acquisition of a 600 MHz NMR Spectrometer for Chemistry, MRI: Acquisition of a High Intensity Single Crystal X-ray Diffractometer, G4421890870, G454325550
OpenAlex ID: W4392763805
FWCI: 1.535
Cites: 29
Cited by: 11
Related to: 10